Pyrazolone dyes and process of making them.



UNITED STATES PATENT orrion.

PAUL JULIUS AND ERNST FUSSENEGGER, 0F LUDWIGSHAFEN-ON-THE-RHINE, GER.- MANY, ASSIGNORS TO BAIDISOHE ANILIN & SODA FABRIK, OF LUDWIGSHAFEN-ON- THE-RHINE, GERMANY, A CORPORATION OF GERMANY.

PYRAZOLONE DYES ANI) PROCESS OF MAKING THEM.

No Drawing.

To all whom it may concern:

Be it known that we, PAUL JULrUs and ERNST FUSSENEGGER, doctors ofphilo'sophy and chemists; subjects of the Emperor of Austria-Hungary, residing at Ludwigshafenon-thelthine, Germany, have invented new and useful Improvements in Pyrazol one Dyes.

and Processes of Making Them, of which the following is a specification.

We have discovered that 3-chlor-2-amino- 1-1nethyl-benzene-5-si1lfonic acid can be employed in the production of new coloring matters which possess a constitution cor responding to the formula N a nooo-ti oH-N=N-R,, in which either R, or R or both, represent the 2-methyl-6-chlor-benzene-4-sulfonic acid residue.

The coloring matters of the formula in which R and R both represent the said residue can be obtained, for instance, by com: bining dihydroxy-tartaric acid with two molecular proportions of the hydrazin of 3-chlor -2- amino-1-methyl-benzene-5 -sulfonic acid. It is preferred to produce those in which R and R differ from one another by acting with a hydrazin on oxalyl-acetic ester and then upon the compound containing the pyrazolone ring formed with a diazo com pound. For the purposes of our invention,

I either the hydrazin, or the diazo, compound,

Spec ification of Letters Patent.

Patented Sept. 28, 1909.

Application filed June 22, 1909. Serial No. 503,633.

tion for British Letters Patent No. 1245 A. D. 1909.

Our new coloring matters consist, when dry, of yellow powders, they are soluble in water yielding from yellow to greemyellow solutions, they dye wool yellow and in the form of their lakes possess a yellow color and are fast to light and upon reduction with tin and hydrochloric acid they yield a pyrazolone of a constitution corresponding to the formula and an 'amin of-a constitution corresponding to the formula R NI-I one at least of the groups R and R being 2-methyl-6-ch1or-benzene--sulfonic acid. The coloring matter which we desire to be understood as claiming specifically is that in which both R and R represent the Q-methyl-6-ohlor-benzene-4- sulfonic acid residue. It yields a greenish yellow solution in water.

The following examples will serve to illustrate further the natureof our invention and how it can be carried into practical efiect, but the invention is not confined to these examples. The parts are by weight.

Example 1; Stir eleven parts of the sodium salt of dihydroxy-tartaric acid with fifty parts of water, and add a suspension of twenty-four parts of the hydrazin of 3-chlor- 2-amino-l-methyl-benzene-5-sulfonic acid in fifty parts of water. On heating the mixture, at first to about fifty degrees centigrade and then, gradually, to from seventy, to eighty, degrees centigrade, solution gradually takes place. The coloring matter can be isolated by precipitation with common salt, or with potassium chlorid, if desired, after having acidified the solution. Filter ott the coloring matter, and press and dry it. It gives rise to lakes which possess very pure lemon-yellow shades of excellent fastness against the action of light.

l lxaniple2z Diazotiaetwenty-two and onefifth parts of 3-chlor-2-an1ino-1-n1ethyl-benzene-5-sulfonic acid in the usual manner and allow the solution to run. while stirring, into a concentrated solution of thirty parts of l para sulfo-pl1enyl-5-pyrazolone-S-carboxylieacid, to which suITieient sodium carbonate has been added to maintain the whole 1. The process of producing colorin matters of the pyrazolone group by com ining dihydroxy-tartaric acid with two molecular proportions of the hydrazin of 3-chlor-2 amino-1-methyl-benzene-5-sulfonic acid.

2. The new coloring matters of the pyrazolone group which consist when dry of yellow powders, are soluble in Water yielding from yellow to green-yellow solutions, dye wool yellow and in the form of their lakes possess a yellow color and are fast to light and upon reduction with tin and hydrochloric acid yield a pyrazolone of a constitution corresponding to the formula 1100c -p=1 :-i-m-oo-on.i-zn

and an amin of a constitution corresponding to the formula R .NH one at. least of the groups R and R, being 2-methyl-6-chlorbenzenel-sulfonic acid.

3. The new coloring matter of the pyrazolone group which consists when dry of a yellow powder, is soluble in water yielding a greenish yellow solution, dyes wool yellow, in the form of its lakes possesses a yellow color and is fast to light, and upon reduction with tin and hydrochloric acid yields a pyrazolone of a constitution corresponding to the formula and an amin of a constitution corresponding to the formula R .NH both of the groups R and R being 2-methyl-(l -chlor-benzenclsulfonic acid. r

In testimony whereof we have hereunto set our hands in the presence of two subscribing witnesses.

PAUL JULIUS. ERNST FUSSENEGGER. Witnesses:

ERNEST F. EHRHARDT, J. ALEC. LLOYD. 

